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S0441

Sigma-Aldrich

SB-366791

≥98% (HPLC), powder

Synonym(s):

N-(3-Methoxyphenyl)-4-chlorocinnamide

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About This Item

Empirical Formula (Hill Notation):
C16H14NO2Cl
CAS Number:
472981-92-3
Molecular Weight:
287.74
MDL number:
MFCD01033818
UNSPSC Code:
12352200
PubChem Substance ID:
24278690
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear

originator

GlaxoSmithKline

SMILES string

COc1cccc(NC(=O)\C=C\c2ccc(Cl)cc2)c1

InChI

1S/C16H14ClNO2/c1-20-15-4-2-3-14(11-15)18-16(19)10-7-12-5-8-13(17)9-6-12/h2-11H,1H3,(H,18,19)/b10-7+

InChI key

RYAMDQKWNKKFHD-JXMROGBWSA-N

Gene Information

human ... TRPV1(7442)

Application

SB-366791 has been used as a transient receptor potential cation channel subfamily V member 1 (TRPV1) antagonist:
  • to infer the in vitro and in vivo pharmacology of (E)-3-(4-t-butylphenyl)-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acrylamide (AMG 9810)
  • to study its effects on sodium hydrogen sulfide (NaHS) or capsaicin-induced contractile activity
  • to study the inhibitory potency of phoneutria toxin (PnTx3-5) (native and recombinant) on various responses mediated by transient receptor potential cation channel subfamily V member 1 (TRPV1)

Biochem/physiol Actions

SB-366791 might exhibit analgesic properties on bone cancer-related pain behavior.
Vanilloid receptor-1 (TRPV1) antagonist.

Features and Benefits

This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Mauricio Guzmán et al.
Immunology, 161(2), 148-161 (2020-07-24)
Dry eye disease (DED) is a highly prevalent ocular surface disorder with neuroimmune pathophysiology. Tear hyperosmolarity (THO), a frequent finding in affected patients, is considered a key element in DED pathogenesis, yet existing animal models are based on subjecting the
SB366791, a TRPV1 antagonist, potentiates analgesic effects of systemic morphine in a murine model of bone cancer pain
Niiyama Y, et al.
British Journal of Anaesthesia, 102(2), 251-258 (2009)
Narender R Gavva et al.
The Journal of pharmacology and experimental therapeutics, 313(1), 474-484 (2004-12-24)
The vanilloid receptor 1 (VR1 or TRPV1) is a membrane-bound, nonselective cation channel expressed by peripheral sensory neurons. TRPV1 antagonists produce antihyperalgesic effects in animal models of inflammatory and neuropathic pain. Here, we describe the in vitro and in vivo
Elizete Maria Rita Pereira et al.
Neuropharmacology, 162, 107826-107826 (2019-10-28)
Capsaicin, an agonist of TRPV1, evokes intracellular [Ca2+] transients and glutamate release from perfused trigeminal ganglion. The spider toxin PnTx3-5, native or recombinant is more potent than the selective TRPV1 blocker SB-366791 with IC50 of 47 ± 0.18 nM, 45 ± 1.18 nM and 390 ± 5.1 nM in
Y Niiyama et al.
British journal of anaesthesia, 102(2), 251-258 (2008-11-29)
Bone cancer pain has a major impact on the quality of life of cancer patients but is difficult to treat. Therefore, development of a novel strategy for bone cancer pain is needed for improvement of the patient quality of life.
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